Auto-Tagging the Post Archive

Since I finished migrating my site from Next.js/Payload CMS to Astro, I’ve been wanting to redo the tag taxonomy for my posts. They’d gotten out of hand over time, and the tag tumbleweed grew to more than 80 tags. What the hell was I thinking when I had both “product design” and “product designer”?

Anyway, I tried a few programmatic ways to determine the best taxonomy, but ultimately manually culled it down to 29 tags. Then, I really didn’t want to have to manually go back and re-tag more than 350 posts. So I turned to AI. It took two attempts. The first one that Cursor planned for me used ML to discern the tags, but that failed spectacularly because it was using frequency of words, not semantic meaning.

So I ultimately tried an LLM approach and that worked. I spec’d it out and had Claude Code write it for me. Then after another hour or so of experimenting and seeing if the resulting tags worked, I let it run concurrently in four terminal windows to process all the posts from the past 20 years. Et voila!

I spot-checked at least half of all the posts manually and made some adjustments. But I’m pretty happy with the results.

See the new tags on the Search page or just click around and explore.